


Perfect Arrangement

by purgatoan



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Barebacking, Bisexual Charlie, Bisexual Dean Winchester, Bisexual Sam Winchester (Campbell), Drag King Charlie, Drag Queen Dean, Established Charlie/Dean Winchester, F/M, Fluff, M/M, Manager Sam, Multi, Oral Sex, Sam is basically Sam Winchester; just not related to Dean, Smut, Strangers to Lovers, Switch Dean, Top Sam, Vaginal Fingering
Language: English
Status: Completed
Published: 2017-03-07
Updated: 2017-03-07
Packaged: 2018-09-30 16:03:33
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,319
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10166660
Author URL: https://archiveofourown.org/users/purgatoan/pseuds/purgatoan
Summary: Dean and Charlie are married. They couldn’t be happier, performing as Rose and Jack, and taking care of their daily lives. One day, Samuel Campbell, one of the big fish in the industry, offers to become their manager. However, he soon transforms from the manager to a friend and undeniable attraction between all of them seems to push them into a state that everyone could easily describe as more than friends.





	

**Author's Note:**

> First time writing this pairing and first time writing such an AU! First things first? I absolutely love this piece, with all my heart. Like, no joke at all. So, I hope you’re going to enjoy!
> 
> Also, I’d love to hear what you think of this one, guys! It’s been a lot of work to put this together so every opinion matters a lot!
> 
> (And, unbeta'd, so all the mistakes are mine!)

“Get your ass here, we have to be ready soon!” Charlie shouted as she was slicking her hair back, her new shortcut proving to be more of convenience if it came to getting ready for the performance.

As she glanced at herself in the mirror, she didn’t see her usual self. The black suit, white dress shirt, dark brown suspenders and black oxfords always went well with how Charlie wanted to look like for the performance, and she always needed to look like a perfect gentleman.

She was lucky not to have much curves, so she didn’t have to hide them for the show. After all, she had to look as convincing as possible. Her stage name was Jack (yes, she came up with it in the middle of rewatching Titanic). Plain and simple, but she liked it nonetheless. Jack was like a part of her that she never showed to anyone and performing as him gave her so much freedom she never thought she had.

The watch on her hand was showing that they had only twenty minutes left before they had to go onto the stage and Dean still didn’t get inside the wardrobe room. He was late as usual.

Honestly, at that point Charlie had no idea how she survived with him for so long, but she’d never trade his stupid ass for anyone else’s. He was her everything, period. Even if he drove her up the freaking wall at least ten times a day.

Fortunately, the door opened soon, hitting the wall with much force, and Dean got inside the room, scrambling to put on the dress and the rest of the clothes for the performance.

“Shit,” he mumbled under his breath as he kept fishing in the drawers to find something, maybe tights?

Charlie rolled her eyes and turned around in the makeup chair to look at her husband, “Finally. Thought you wouldn’t show up.”

“Of course I would show up. I always do, it’s my show too, after all,” he responded with a smile, sliding sheer black stockings onto his legs.

Charlie got up from the chair and went to one of the drawers, pulling out her make up bag. They had around fifteen minutes left, Dean wasn’t dressed yet, and she still had to put on some makeup on his face.

Fortunately, Dean was quick at getting dressed and, in no time, he was sporting an outfit similar to the one Freddie Mercury was wearing in the video to Queen’s I Want To Break Free. That was supposed to be his number for that night. Cliche, but Dean liked Queen. Sue him.

“Okay, princess. Pretty me up,” Dean joked as he walked to the makeup chair and sat down, his heels clicking on the tiled floor. It was a nightmare to learn to walk in them, but after so many years of being a Drag Queen Dean had it down perfectly.

“You’re already handsome, you dork,” Charlie retorted, pulling Dean in for a kiss that lasted way too short for her liking, but they didn’t have time.

Primer, foundation, contouring, powder, blush, you name it. Charlie was an expert at making Dean look like a goddess for the show and it might’ve been one of the many reasons he loved her so much. Guess he was lucky that they’ve met while on a tour, at least he wasn’t afraid that Charlie would make fun of his hobby that soon turned into a part-time job.

It was definitely freeing for Dean as well to dress up, go onto the stage, and be someone completely different than Dean Winchester. He could let his imagination run wild as he was preparing his gigs and it never hurt to have some fun and laugh a bit.

As he and Charlie got together, he changed his stage name to Rose, partly to annoy her (he was the Rose to her Jack, apparently), but also to show he wasn’t afraid to admit he loved chick flicks, Titanic included.

Soon, they were both ready, and he slipped a black wig onto his head before they headed out onto the stage.

* * *

The song was a complete success and the public was amazed by how well Dean (or rather, Rose) performed. His voice was a feature that he was proud of but never showcased before, but he knew that would bring him more invites for other shows. Who would’ve thought that singing in public would be so fun?

Dean came to a conclusion that listening to Charlie wasn’t that bad after all. She had kept bragging about how well he would fit for that one and, now that it was over, he was glad he had said yes.

* * *

The only downside of being a Drag Queen (not that much like being a Drag King) were people that thought this type of art had something to do with other things than performance. For example, sometimes Dean was being met with arguments such as he wasn’t a man anymore or that he wasn’t manly enough, because of the fact he enjoyed performing as Rose. It was complete bullshit, obviously, but it still stung a bit. Why people couldn’t wrap their mind around a concept that it was just for fun and didn’t mean anything else?

That’s why Dean grew to be wary of people that tried to approach him on the streets or somewhere else that he didn’t feel safe in and ask about his stage career. It was only a cautious step, nothing ever happened to him fortunately, but he had heard of terrible things happening to his other friends that performed. Better safe than sorry, after all.

* * *

After most of the performances there were parties on which all people from the industry could hang out, talk about their ideas for the future shows, share tips and tricks, and let’s not forget that the alcohol was always free. It made for a perfect combination.

Dean and Charlie were currently getting out of the party; it was late and they both wanted to get home by the midnight. They were lucky they lived so close to the club they were performing at; most of the people didn’t have that luxury and had to drive a long way there. Charlie was a bit buzzed, Dean was sober (he had to drive home after all), and they were heading toward their car, the beautiful Impala.

As they got into the parking lot they noticed a tall man running toward them. He was shouting for them to wait, his voice a bit ragged.

“Get inside, I’ll see what he wants.” Dean told Charlie, taking pepper spray out of the glove compartment, then shoving it into his jacket’s pocket. She obliged, locking the door afterward.

When the man caught up to them, he waited a bit before he regained his ability to speak, then let out, “Dean and Charlie Winchester, right?”

“Depends on who’s asking,” Dean reached to his pocket for the pepper spray, his fingers sliding over the smooth plastic.

“Oh, I’m sorry. I was so thrilled about seeing you guys I forgot to introduce myself,” the man smiled, dimples appearing on his face. Then, he extended his hand toward Dean, “Sam Campbell, manager.”

Dean let out a sigh of relief as he heard that surname. Campbell was one of the big fish in the industry and to see that he wanted to talk to Dean and Charlie could mean that great things were waiting for them.

He shook Sam’s hand and smiled, actually taking in how the guy looked. Apart from the obvious being tall part, he was actually quite cute, and it was rare of Dean Winchester to consider anyone but his wife cute.

Strange.

Also, Dean picked up on the fact that the guy must’ve been pretty well-built, considering how tight fitting his button up shirt was. It surely was a miracle it didn’t tear on his muscles.

Seems like Dean’s bisexuality decided to make appearance yet again.

“I’ve heard great things about you, I’ve gotta say,” Dean admitted after letting go of Sam’s hand. Really big and soft hand.

And another dimpled smile appeared, “Really? Awesome, because it might help me with trying to convince you to work with me.” Sam raised his eyebrows at Dean, this time sporting a one-sided smirk.

“I don’t think a lot of convincing will have to be done,” Dean shrugged, making Sam chuckle, “but you’d have to wait until tomorrow at least, so I can discuss it with Charlie. She’s not really in the shape to make decisions now,” he pointed to his wife already asleep in the passenger seat, her legs stretched out on the dashboard.

Sam couldn’t help but smile again, “Of course.” Reaching to his jeans pocket, he took out his wallet and pulled out a business card, then handed it to Dean. “Call me when you’re ready.”

“Will do.” Dean mock-saluted as Sam turned around and began walking away.

* * *

The following morning Dean and Charlie talked through all the pros and cons of having a manager and they came to a conclusion that they could use one, actually. Taking care of everything shows-related has been taking up a lot of their time and, considering they both had jobs outside of performing, it was quite difficult not to get lost in everything.

Phone calls were made, a meeting was scheduled (even though the word meeting sounded a bit too serious, if someone were to ask Dean), and neither of them could wait to get that arrangement going.

* * *

“So, what’s the verdict?” Sam joked as he got inside the cafe and sat on the chair opposite to Dean and Charlie.

“We’re in!” Charlie beamed, making a few people in the cafe turn around and look at her. “I mean, it’d be an honour to work with you, Mr. Campbell.” She blushed under the gaze of their soon-to-be manager.

“Please, call me Sam.” He said simply and she nodded furiously, opening her mouth like she wanted to say something, then closing it abruptly.

Dean rarely saw her as nervous as she was in that moment and he couldn’t help but wonder why she was acting like this. Charlie was incredibly excited for the contract, she mentioned she would feel like a real star with a manager, but it couldn’t have been only excitement. It was something else.

Dean made a mental note to ask his wife about this later.

As they were chatting with Sam about the conditions of the contract they’ve fallen into an easy routine of the conversation, like they knew him for ages. Sam was a really nice guy and, apart from the fact he was sweet and attractive, he was also funny and adorable as hell. It would be fitting to compare him to a giant puppy.

Also, Dean found himself staring at Sam more often than not, either eyeing his gorgeous face or muscular body, all kinds of dirty thoughts racing through his mind. How it would feel to be pinned down by Sam, how it would feel to dig fingers into those steel hard muscles. So many ideas.

He definitely had to talk to Charlie about this.

Fortunately, in their relationship there was never such thing as drama over crushes or people one of them found attractive. None of them had problems with voicing their thoughts; sometimes they even bragged about how hot someone was, some girl or a guy that they saw pass them by.

However, they never thought it would happen with a person that wasn’t a stranger, but who would become a constant part of their lives.

* * *

When Dean blurted out to Charlie they needed to talk (at the same time that Charlie let out that they had to talk) right after they got back home from the meeting, there was no hiding it anymore. It turned out they both found Samuel Campbell a fine specimen. But, what were they going to do about it? That was a matter they had yet to discuss.

Working with Sam turned out to be a blessing for both of them. They stopped forgetting about the shows, they didn’t have to look for new places to perform, they didn’t have to worry about the wardrobe or other things needed for a certain spectacle. Sam was taking care of it all and opening new doors in the industry at the same time, being able to work them into larger and larger shows that attracted more people and, what came with it, brought more money.

Every dollar spent on that arrangement was definitely worth it.

Soon, Sam transformed from an employee into a friend and they were both happy with that change. Though it crossed out the initial idea that they had for a threesome; it’d definitely make things awkward between them.

But, it had lots of perks. Instead of meeting somewhere public to discuss new terms or ideas he’d simply come to their house. They’d hang out, watch some movies and drink beer, then end up talking about the arrangement, but also everything in between. Life, jobs, the past, the future, you name it.

They fell into an easy pattern and they couldn’t be happier about it. Frustration and tension was still there, though, but fortunately they knew that it wasn’t one sided.

Too many times Charlie noticed Sam blatantly checking Dean out when he was undressing before the show, often wandering around the wardrobe room in nothing but boxers. No one could blame him, really, Dean was practically sex on legs. Or when Dean would put on tight jeans and a henley, that was a panty-dropping (or rather, a boxers-dropping) mix. And Sam fell into that trap without even knowing that it was set specifically for him.

Too many times Dean noticed Sam eyeing Charlie when she was looking for something in the drawers or just walking around. She never wore much when she was around people she felt comfortable with. That’s why, more often that not, Charlie had nothing on but an old, worn out T-shirt that was once Dean’s, along with a pair of boxers that were a bit too tight for Dean’s liking, her perky ass making the fabric stretch quite a bit. Sam was never able to withdraw his gaze from her anytime she showed up dressed in something like this.

Bonus points if they were both dressed like that and doing couple-y things together. It seemed like Sam’s interest doubled in those types of situations.

First time Charlie and Dean barely brushed their lips together in Sam’s presence, Sam blushed like crazy. They pulled away nearly immediately, it was just a peck after all, but he looked like they just shed their clothes and made out in front of his face. It was adorable, really.

They made sure to tease him a bit more after that.

Longing stares, lingering touches, drawn out kisses. It all worked like a charm, making Sam nearly squirm in his seat and even come up with an excuse to leave their house once or twice, his hard-on prominent. Other times, he would zone out and simply stare at them, until one of them cleared their throat. Their plan was working, they just had to wait for the right moment.

And, eventually, that right moment came.

* * *

Again, Charlie and Dean got a bit carried away with one kiss as Sam was at their place. Or, maybe carried away was not enough of a description.

Dean and Charlie were on the couch, watching a movie with Sam, but they found themselves making out heavily during the commercial break. They probably forgot that Sam was even there, too caught up in the moment to even look around.

Charlie was on Dean’s lap, her hands under Dean’s t-shirt, without a doubt feeling up the muscles that were there. Dean was cupping Charlie’s ass, his large hands covering her tiny body. They were gasping and moaning and grinding and it was just too much sexual tension to live through.

Sam was too shocked with what was playing in front of him at first. He was stunned, honestly, but he came to his senses after a minute or so and cleared his throat loudly, trying to ignore the tightness of his jeans after seeing such a performance.

“Shit,” Dean let out as Charlie got up from his lap.

“Whoops,” Charlie added, fixing the t-shirt that has ridden up her belly button at some point.

Sam chuckled nervously, “Yeah. I-I can go if you guys want some time to yourself, just say a word.”

Dean got up from the couch, Charlie followed suit, and they both walked closer to Sam, looking quite intimidated and shy.

“What if we want some time to ourselves and with you?” Dean licked his lips and smiled.

To say that Sam was shocked would be an understatement. “You’re joking, right?”

“Not at all! I mean, if you’re not interested then cool, but we thought you are, so that’s why we’re asking.” Charlie said, then grinned at Sam. He could tell they were completely serious, even giddy with excitement.

“It’s all up to you, honestly.” Dean shrugged, sneaking an arm around Charlie and pulling her closer. “We can pretend this never happened and it’ll all go back to how it used to be. Just friends. No hard feelings.”

Sam couldn’t help but smile, “I definitely am interested, but how is this going to go? Is it just a one time thing or-?” He cut off, waiting for the couple to answer.

“Whatever you want it to be,” Charlie admitted, “Friends with benefits, one time thing, or more, if you’re up for it.”

“Charlie! Don’t overwhelm the guy, give him some time to digest.” Dean let out, surprised, but she just mouthed “what?” at him.

“Okay, okay, alright,” Sam raised his hands in surrender, letting out a chuckle. “I can’t deny I’m crazy over both of you, so I guess more would fit the situation?”

“Perfect!” Charlie beamed, a wide grin on her face.

“Awesome!” Dean let out at the same time, smiling from ear to ear.

After a moment of awkward silence, Sam cleared his throat, “So, what do we do now?”

“Well…” Charlie trailed off, stepping closer to Sam. She took his hand in hers, and he leaned down, letting her pull him in a kiss. She tasted like bubblegum, her lips soft against his, barely there, but the kiss was demanding nevertheless.

Sam opened his eyes for a second, looking at Dean for permission, and when Dean nodded, he got lost in this gorgeous woman. He couldn’t help but trail his hands down the sides of her body, onto her ass, then down to her thighs. Sam picked her up without a second thought and she wrapped her legs around his waist, breaking the kiss eventually when they were both out of breath.

“Wow.” She breathed out, “You’re so huge.” She blushed then and added, “I mean, not in the huge-huge sense, but probably too, and it honestly would be quite awesome if you were, you know?”

“I guess you’ll both see, if you want,” Sam suggested and Charlie licked her lips, then turned a bit to the right to look at her husband.

“What, you’re just gonna stand there and watch?” She teased and Dean laughed, stepping right next to Sam and Charlie.

Dean’s hand went up to rest on Sam’s neck and he pulled Sam in for a lazy kiss. They had all the time in the world, after all. For Sam, Dean tasted quite similar to Charlie, but also a lot differently. More fresh, a bit less sweet, maybe like a fruity-minty chewing gum? Sam could feel Charlie nipping at his jaw, then neck as he kept kissing Dean, and he couldn’t wait to feel more of them both.

When Dean nipped at his bottom lip Sam let out a gasp and let Dean in, going a bit pliant under the couple’s demonstrations. If they were to keep going like this, they should all get somewhere else, or he would turn into mush right there.

“How about moving this all to bedroom, boys?” Charlie suggested, “Not that I mind the view, ‘cause it’s freaking hot, but you know, a bit more comfy?”

Dean pulled away and smiled, “Sure thing. Let’s go, giant.” He added, turning on his feet, and began walking toward the bedroom.

Sam walked after Dean, Charlie clinging to him like a small monkey, and he entered the cozy bedroom right after Dean, closing the door with a bit more force than necessary. But, who could blame him if he was about to fuck and get fucked by two most attractive people in the world?

Dean was already getting out of his clothes and throwing them on the floor hastily, so Sam wasted no time either. Setting Charlie on the bed, he began getting undressed as well and Charlie followed suit, pulling her t-shirt over her head, then peeling leggings of her legs.

In the meantime Dean climbed on the bed, already completely naked, and unclasped Charlie’s bra, helping her out of it. Sam couldn’t hold a gasp that escaped his mouth as he took in her perky breasts and beautiful skin; she was gorgeous. He stepped out of his boxers, his cock heavy between his legs, then crossed the room in a few strides and knelt in front of her, hooking his thumbs in her panties.

She gave him a nod and he slid them down her legs, caressing her smooth skin in the process. Then, Sam tossed them on the floor and slowly spread Charlie’s thighs, and she laid on the bed, giving him permission to move things further.

“Go fast, then slow, then speed up again. Just tease her a bit and she’ll love it,” Dean instructed and Sam nodded, licking a broad stripe from Charlie’s clit and down, short hairs tickling his nose. He repeated it a few times, switching from straight lines to zig-zags, then back to straight lines, first working just with the tip of his tongue, then using all of it to make Charlie tremble under his touch. He was getting hard so fast it wasn’t even funny.

“Damn, you’re a fast learner,” Charlie let out, her breathing ragged.

Dean leant forward and captured Charlie’s nipple in his mouth just as Sam began circling her clit. She couldn’t help but moan as they both began sucking and licking and nipping on her flesh, bringing her to the point of almost-release, then backing out as she was getting too close.

After a while, Sam let go of her clit and moved down, swiping his tongue around her folds then nipping on the skin of her thighs. As he started soothing the sting with his tongue, Charlie started giggling, and he looked up at her and Dean, his eyebrows raised.

“Sorry, it tickles,” She said simply and Sam huffed out a laugh as well.

“Okay, got it,” Sam whispered and got back to work, putting Charlie’s legs on his shoulders, so they wouldn’t get in the way.

Without a second thought, he slid a finger inside her pussy, smiling when he felt how wet she was already. Sam began moving it slowly, in and out, and resumed sucking on her clit, alternating between moving fast and slow, just like Dean told him. After some time, he added another one, scissoring them and grazing Charlie’s walls with his fingertips once in awhile, enjoying the way she was squeezing his digits. It didn’t take long and she was begging for more, pleading both of them to do more, to give her more.

More, just more.

And who would they be to say no to such a polite request?

They both sped up their movements and even if neither of them set a specific rhythm, it didn’t matter that much. Under Sam’s skilled fingers and expert tongue, under Dean’s fingers, playing with one of her nipples and his mouth that was ravishing the other one, she came apart. Her wetness coated Sam’s fingers and tongue, a litany of _ohmygodyespleasefuck_ spilling from her lips as she rode out her release.

“Holy shit,” Charlie let out as she came down from her high, her chest heaving in time with her breaths.

Sam couldn’t help but grin as he got up from the floor, his knees a bit numb from being in one position for a bit too long, “I’m gonna take it as a compliment.”

“You definitely should, man.” Dean added, winking at Sam, then pulled his wife in for a short kiss. After pulling away, he eyed Sam, licking his lips, then turned his attention to Charlie, “So, how do you want us, babe?”

Charlie pushed herself up on her hands to a sitting position and bit her lip, her intense gaze almost making Sam squirm. “How about this one? You’re gonna fuck me and, at the same time, Sam will fuck you?”

Sam felt his mouth go agape at those few words and his cock twitch at the thought of getting to fuck Dean. Charlie was beautiful, of course, and he would love to do nothing but make her come on his cock over and over again, but if he were to say he wasn’t fantasizing about Dean even more he’d be lying.

Those damn bowlegs, this stupid smirk, those vibrant emerald greens, those muscular arms looking like they were about to rip every tight t-shirt he was wearing. Yes, there was definitely a lot that Sam wouldn’t mind to look at or touch or kiss or more.

Dean only shrugged, like this suggestion didn’t surprise him at all, “Sure, sweetheart. You cool with this, Sam?”

“More than cool, actually,” Sam admitted, feeling his cheeks heat up a bit.

Dean couldn’t help but grin, “Awesome.” Then he made a come-hither motion at Sam with his left hand and ran the fingers of his right hand down Charlie’s spine, saying, “Okay. Scoot over, Hermione, I got to taste him.”

She rolled her eyes at that and got up from the bed, walking over to one of the drawers that were in the room. Before Sam had a chance to ask what Charlie was looking for, Dean palmed Sam’s cock, efficiently making all the rational thoughts leave Sam’s mind.

“Such a nice dick you’ve got here,” Dean praised, making Sam blush, then opened his mouth and swept his tongue over the slit, the action earning him a gasp from Sam.

Then, there was no holding back or trying to keep the reactions under control as Dean began licking the underside of Sam’s cock, not following any pattern or a scheme, just licking and kissing and sucking and it was perfect. It was messy and disorganised, but amazing nonetheless, and Sam couldn’t hold back a moan as Dean opened up and took as much of Sam’s cock as he could.

It was a struggle for Sam not to thrust his hips forward, especially when Dean swallowed repeatedly around him, but he didn’t want to overstep or cause Dean any discomfort. Even if his mouth was so wet and warm and his tongue was licking in all the right spots. Even if Sam had the best view in the world and Dean’s gaze was constantly locked with his, those emerald orbs captivating and mesmerizing, consuming Sam whole, making Sam’s head hazy with desire.

Then, Sam heard light steps from behind him, and knew that Charlie must’ve been watching them. There was no way she was looking for something for so long, right? He felt her fingers graze his bicep, making him shiver under her touch, and only then he realized he had raised his hands up to tangle them in Dean’s hair, but didn’t do that for no particular reason. It was probably safe to assume that he was too caught up with what Dean was doing and, honestly, he wasn’t surprised at all.

“What?” Charlie let out as Dean let go of Sam’s cock and turned his attention to her, “I’ve had a great view, it would be a shame not to look at you two for a bit.” She sported a wink in Sam’s direction, making Sam smirk, and went to the other side of the bed, sitting on Dean’s thighs afterward. Sam spotted a bottle of lube in her hands.

“You’ll get me ready for this monster, huh?” Dean teased, raising from the bed to pull Charlie in for a kiss, throwing her off his thighs in the process. She complied, though, eagerly linking her mouth with his, but pulled away fairly quickly, making Dean let out a whine.

“Yup, but get back to sucking, or I will,” Charlie ordered, and Dean shook his head, letting out a laugh.

He laid back on the bed, resuming his previous position, and grasped Sam’s cock again, “As you wish, babe,” then opened his mouth, taking Sam as deep as he could without gagging, then bobbing up and down, his tongue swirling around Sam’s length.

From where he was standing, Sam could see Charlie pouring lube onto her fingers and she shot him a mischievous smile as she began working Dean open. Dean stopped working on Sam’s cock for a short while, his back arching a bit as Charlie started wiggling one finger inside him. After taking a deep breath, he began licking and sucking again, but his rhythm kept stuttering every time she went a bit deeper.

Honestly, Sam didn’t mind slow pace and all the teasing, because he didn’t want to come too soon. Dean was too good at what he was doing and the fact that he couldn’t concentrate that well on making Sam feel perfect all the time was actually great, because Sam swore he could come at the thought alone of what was going to be next.

Then, Dean started moaning as Charlie slid another finger inside him and Sam couldn’t help but stutter a bit forward with his hips, the head of his cock hitting the back of Dean’s throat. He backed away quickly, but Dean gagged anyway, and what was surprising, he didn’t tap out at all. Dean just took a deep breath, backing away a bit, and got back to sucking and licking and swallowing, making Sam tremble as he felt his orgasm slowly approaching.

“Dean…” Sam stuttered, “Stop, or I’m going… I’m gonna come.”

Dean let out a whine, but obliged, and released Sam’s cock with a loud pop. Then, he dragged his tongue over Sam’s length and over Sam’s balls, like he couldn’t bring himself to stop, like he couldn’t get enough of his taste.

However, it was long forgotten when Charlie slid another finger, already the third one, in Dean’s slicked hole, making Dean arch from the bed and moan loudly.

“More.” Dean ordered and she complied, rutting them deeper and bumping into his prostate. Sam couldn’t help but walk over to the other side of the bed, he had to see how it looked like from the other angle.

Sam let out a gasp as he saw how effortlessly Charlie’s fingers were being pushed into Dean. He picked up a bottle of lube from the bed and slicked his fingers as well, sliding one in alongside Charlie’s, stretching Dean out even more.

They started moving together, Charlie sliding in, Sam sliding out, and Dean kept trashing on the bed, overwhelmed with the amount of pleasure those two were bringing him. He couldn’t keep whines and moans and loud _yespleasemore_ from spilling from his lips and it did nothing but spur Charlie and Sam on.

Eventually, Charlie’s four fingers and Sam’s two fingers were inside Dean, wiggling and moving around with ease. Deciding that he was ready to take Sam, Charlie slid her fingers out of Dean’s loosened hole and Sam followed suit, retracting his fingers as well. Neither of them missed the fact that Dean had clenched around them right before they slid their fingers out, like he desperately didn’t want to go back to being empty.

“Someone’s greedy,” Charlie sing-songed, playfully slapping Dean’s right asscheek.

“Someone’s being an ass and doesn’t do what I politely ask them to do,” Dean retorted, getting up from the bed, making Charlie roll her eyes at him.

Sam couldn’t help but laugh at their exchange and they both turned their attention to him, which made him laugh even more, “What? I just, I don’t know, I didn’t expect it all to be so…”

“Normal?” Charlie butted in.

“Easy?” Dean let out at the same time.

Sam nodded, “Yeah. Pretty much.”

“Well, that’s good. We wouldn’t want you to feel intimidated or weird, you know?” Dean admitted as Charlie rolled to her back, spreading her legs wide.

Still, Sam couldn’t help but blush as she bared herself for them again, “Y-yeah, about that…”

Dean let out a laugh, “Dude, you’re still shy? Even after what you did to her and what I did to you?”

“Come on, give Sam a break,” Charlie scolded, “And I’m going to die from boredom here,” She teased, challenging them both.

“Fine,” Dean rolled his eyes in fake annoyance, and got on the bed, setting himself in between Charlie’s legs, “You clean, Sam?”

Sam didn’t hesitate before answering, “Absolutely.”

Dean nodded, “Good. Go in bare, come on.” Then, he gestured for Sam to hop on the bed as well, and Sam got on, then knelt right behind Dean, putting his hands on Dean’s hips.

“Charlie, get your legs up a bit, it’ll be easier,” Sam suggested and she complied, resting them around Dean’s waist.

With one swift move, Dean bottomed out in Charlie, and she tightened her hold on him, like she wanted to push him even further inside her pussy. Sam waited a moment, then lined up his cock at Dean’s hole and began slowly driving in, letting Dean get used to the feeling. It wasn’t that easy though, as Dean’s walls kept fluttering around Sam’s cock, and he wanted nothing but to go all the way in. It felt so good he knew he’d lose control soon.

“I’m not gonna break,” Dean breathed out, his voice low and raspy, and that was all the encouragement that Sam needed.

He bottomed out, making both Charlie and Dean moan loudly, then pulled out slowly, his cock dragging over Dean’s prostate. Without a second thought, Sam thrusted back and pushed Dean even deeper into Charlie.

“Holy…” She let out, but didn’t have the time to finish this one as Sam repeated this movement again, his pelvis flush against Dean’s ass. Dean backed away a bit, fucking himself onto Sam, and she couldn’t help but whine as he was pushed back inside her when Sam stuttered his hips forward.

They picked up their pace, without that much of a rhythm, but with much eagerness, and that was enough to turn all three of them into a complete mess, everyone impatient to get their release.

Sam started nibbling on Dean’s muscular shoulders, enjoying the way Dean was squirming under him as his teeth were grazing Dean’s skin. It seemed like nothing was enough for Dean as he kept impaling himself on Sam’s cock, curses spilling from his lips every time it hit his prostate. Charlie could do nothing but hold on as Dean’s cock was driving deep into her, her walls clenching repeatedly around it, her legs trembling and nearly numb from being up for so long.

Sam’s cock was throbbing inside Dean more and more with every passing second and Dean started moving even faster, as they were all impossibly close, right on the edge. He could barely feel his legs from being in this position for so long, but he didn’t stop, using Sam’s momentum to push him even further. As Charlie’s back arched from the bed, his hand dropped down to rub on her clit without a second thought, like an instinct. It didn’t take long, she came within moments really, triggering his release. Dean couldn’t help but shout, her walls squeezing his cock like a vice, tight and perfect, just like always.

As Dean was filling her, his cock shooting spurt after spurt of come inside her pussy, he felt Sam come as well, wet and warm in his ass, to the point that come was leaking out of his hole. He didn’t mind at all, rather enjoyed being stretched out so hard that he was sure he would feel it for days to come. And the fact he loved being marked as someone’s was a completely different story.

They slumped into a pile on the bed, too tired to even lift a finger. It wasn’t comfortable at all, though, as Charlie was the one on the bottom and they were both trying not to put all their body weight on her, their arms cramping from how long they’ve been holding themselves up.

“You mind moving or something? I’m so sore,” Charlie suggested, groaning, and Dean couldn’t help but grin.

“Sure thing, princess, but you’re not the only one sore in here,” Dean teased, letting out a whine as he felt Sam’s cock slide out of his hole.

He felt Sam’s hand linger on his ass as Sam got up from the bed and said, “Hope it’s a good kind of sore.”

Chuckling, Dean slid out of Charlie and responded, “Definitely.”

Dean rolled to the side and pulled Charlie closer, planting a soft kiss on her forehead. In no time, Sam scrambled on the bed as well and laid on Dean’s other side, slinging his arm over Dean’s chest. They laid like this for awhile, simply enjoying the way they all seemed to fit together like pieces of a puzzle.

“You planned this, didn’t you?” Sam wondered, nuzzling into Dean’s neck.

The laugh that Charlie and Dean let out was enough of an answer.


End file.
